[ CAS No. 904326-88-1 ]

Name: 904326-88-1|N-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-amine|98%
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SKU: A847562
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Quality Control of [ 904326-88-1 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 904326-88-1 ]

CAS No. :	904326-88-1	MDL No. :	MFCD11878345
Formula :	C₁₁H₁₈BN₃O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	QDOXNCAIXITTKA-UHFFFAOYSA-N
M.W :	235.09 g/mol	Pubchem ID :	46739641
Synonyms :

Safety of [ 904326-88-1 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P261-P264-P271-P280-P302+P352-P304+P340+P312-P305+P351+P338-P332+P313-P337+P313-P362-P403+P233-P405-P501	UN#:
Hazard Statements:	H315-H319-H335	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 904326-88-1 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 904326-88-1 ]

[ 904326-88-1 ] Synthesis Path-Downstream 1~17

Yield	Reaction Conditions	Operation in experiment
50%
50%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 85℃; Inert atmosphere;	39.39b Step 34b: N-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetamide (Compound 0602-107) General procedure: Step 34b: N-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetamide (Compound 0602-107)[0334]To a solution of compound 0601-107 (2.5 g, 11.6 mmol) and bis(pinacolato)diboron (4.4 g, 17.5 mmol) in dioxane (100 mL) was added potassium acetate (3.4 g, 35 mmol) and PdCl2(dppf)2 (0.95 g, 1.1 mmol). The mixture was degassed with nitrogen and heated at 85° C. for overnight. The reaction mixture was concentrated under reduced pressure to afford the crude product, which purified by column chromatography (ethyl acetate in petroleum ether, 15% v/v) to give the compound 0602-107 (1.55 g, 51%) as a pink solid. LCMS: 262 [M+1]+. 1H NMR (400 MHz, DMSO-d6) δ 1.29 (s, 12H), 2.03 (s, 3H), 7.30 (s, 1H), 7.31 (d, J=2.0 Hz 1H), 7.73 (d, J=2.0 Hz, 1H), 7.89 (d, J=1.6 Hz, 1H), 9.93 (s, 1H).
50%	With palladium bis[bis(diphenylphosphino)ferrocene] dichloride; potassium acetate In 1,4-dioxane at 85℃; Inert atmosphere;	39b N-(3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) acetamide (Compound 0602-107) General procedure: Compound in dioxane (100mL) 0601-107 (2.5g, 11.6mmol) and a solution of bis (pinacolato) diboron (4.4 g, 17.5 mmol), potassium acetate (3.4 g, 35 mmol) and and PdCl2 (dppf) 2 ( 0.95g, 1.1mmol) was added. The mixture was degassed with nitrogen and heated overnight at 85 ° C.. The reaction mixture was concentrated under reduced pressure to give the crude product, which was purified by column chromatography (petroleum ether in ethyl acetate, 15% v / v) to give the compound 0602-107 as a pink solid obtained (1.55 g, 51%).

2
[ 31402-54-7 ]
[ 73183-34-3 ]
[ 904326-88-1 ]

Yield	Reaction Conditions	Operation in experiment
100%	With potassium acetate In N,N-dimethyl-formamide at 80℃; for 2h; Inert atmosphere;	18.2 N,N-Dimethylformamide (20 ml) was added to 5-bromo-N-methylpyrimidin-2-amine (3.0 g, 16.0 mmol), bispinacolatodiboron (4.86 g, 19.2 mmol), and potassium acetate (4.7 g, 47.9 mmol) and the atmosphere in the reaction vessel was substituted with nitrogen. A 1,1'-bis(diphenylphosphino)ferrocene]palladium (II) dichloride dichloromethane complex (650 mg, 0.80 mmol) was added, the atmosphere in the reaction vessel was substituted with nitrogen again, and the resulting mixture was stirred at 80° C. for 2 hours. The reaction mixture was partitioned with ethyl acetate and saturated brine and filtrated through celite and the organic layer was washed twice with saturated brine and dried over magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel chromatography (hexane:ethyl acetate=8:2 to 6:4) to give the title compound (3.8 g, 100%) as a white solid.1H-NMR (CDCl3) δ: 1.32 (12H, s), 3.03 (3H, d, J=5.12 Hz), 5.66 (1H, brs), 8.58 (2H, brs).
82%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 115℃; for 5h; Inert atmosphere;	20 /V-methyl-5-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)pyrimidin-2-amine (i 12): /V-methyl-5-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)pyrimidin-2-amine (i 12): To a stirred solution of 5-bromo-/V-methylpyrimidin-2-amine (0.5 g, 2.65 mmol) in dioxane (10 ml_), bispinacolatodiboron (0.81 g, 3.19 mmol) and KOAc (0.39 g, 3.97 mmol) were added and the reaction was degassed with argon for 20 min. PdCI2(dppf) (0.19 g, 0.26 mmol) was then added and the reaction mixture was purged with argon for another 10 min. The reaction was heated at 1 15°C for 5h. The progress of the reaction was monitored by TLC. After completion, the reaction mixture was diluted with ethyl acetate, filtered and filtrate was concentrated under reduced pressure to afford /V-methyl-5-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)pyrimidin-2- amine (i12) (0.5 g, 82%). MS (ESI) m/e (M+1 )+: 236
64%	With potassium acetate In 1,4-dioxane at 115℃; for 4.25h; Heating / reflux;	2 [0240] To a dry 50O mL flask was added 2-methylamino-5-bromopyrimidlne(9.5 g, 50.5 mmol), potassium acetate (15.1 g, 154.4 mmol), 4,4,5,5,-tetramethyl-2- (4,4,5,5,-tetramethyl-l,3,2-dioxaborolan-2-yl)-l,3,2-dioxaborolane (14.1 g, 55.5 mmol) and dioxane (280 mL). Argon was bubbled through the solution for 15 minutes, at which time l,l'-bis(diphenylphosphino)ferrocene palladium(H) chloride dichloromethane adduct (2.05 g, 2.51 mmol) was added. The reaction was refluxed in a 115 0C oil bath for 4 hours under argon. After cooling to room temperature, EtOAc (500 mL) was added and the resulting slurry was sonicated and filtered. Additional EtOAc (500 mL) was used to wash the solid. The combined organics were washed with H2O (2x300 mL), NaCl(Saq, (300 mL), dried over Na2SO4, filtered and the solvents were removed in vacuo. Purification by SiO2 chromatography (50% EtOAc/hexanes) yielded an off white solid (7.66 g, 64%). LCMS (m/z): 154 (MH+ of boronic acid, deriving from in situ product hydrolysis on LC). 1H NMR (CDCl3): δ 8.58 (s, 2H), 5.56 (s, IH), 3.02 (d, 3H), 1.32 (s, 12H).

64%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate In 1,4-dioxane at 115℃; for 4h; Inert atmosphere;
64%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate In 1,4-dioxane at 115℃; for 4h; Inert atmosphere;	2 Synthesis of methyl[5-(4,4,5,5-tetramethyl(l ,3,2-dioxaborolan-2-yl))pyrimidin-2- yl] amine[0085] To a dry 500 mL flask was added 2-methylamino-5-bromopyrimidine (9.5 g, 50.5 mmol), potassium acetate (15.1 g, 154.4 mmol), 4,4,5,5, -tetramethyl-2-(4,4,5, 5,- tetramethyl-l ,3,2-dioxaborolan-2-yl)-l,3,2-dioxaborolane (14.1 g, 55.5 mmol) and dioxane (280 mL). Argon was bubbled through the solution for 15 minutes, at which time l,l'-bis(diphenylphosphino)ferrocene palladium(II) chloride dichloromethane adduct (2.05 g, 2.51 mmol) was added. The reaction was refluxed in a 1 15 °C oil bath for 4 hours under argon. After cooling to room temperature, EtOAc (500 mL) was added and the resulting slurry was sonicated and filtered. Additional EtOAc (500 mL) was used to wash the solid. The combined organics were washed with H20 (2x300 mL), NaCl(sat ), (300 mL), dried over Na2S04, filtered and the solvents were removed in vacuo. Purification by Si02 chromatography (50% EtOAc/hexanes) yielded an off white solid (7.66 g, 64%).LCMS (m/z): 154 (MH+ of boronic acid, deriving from in situ product hydrolysis on LC). ¾ NMR (CDCls): δ 8.58 (s, 2H), 5.56 (s, 1H), 3.02 (d, 3H), 1.32 (s, 12H).

Reference： [1]Current Patent Assignee: DAIICHI SANKYO COMPANY, LIMITED - US2010/130492, 2010, A1 Location in patent: Page/Page column 93
[2]Current Patent Assignee: UCB - WO2016/124508, 2016, A1 Location in patent: Page/Page column 43
[3]Current Patent Assignee: NOVARTIS AG; Novartis (w/o Sandoz) - WO2007/84786, 2007, A1 Location in patent: Page/Page column 90-91
[4]Burger, Matthew T.; Knapp, Mark; Wagman, Allan; Ni, Zhi-Jie; Hendrickson, Thomas; Atallah, Gordana; Zhang, Yanchen; Frazier, Kelly; Verhagen, Joelle; Pfister, Keith; Ng, Simon; Smith, Aaron; Bartulis, Sarah; Merrit, Hanne; Weismann, Marion; Xin, Xiaohua; Haznedar, Joshua; Voliva, Charles F.; Iwanowicz, Ed; Pecchi, Sabina [ACS Medicinal Chemistry Letters, 2011, vol. 2, # 1, p. 34 - 38]
[5]Current Patent Assignee: DANA-FARBER CANCER INSTITUTE - WO2012/109423, 2012, A1 Location in patent: Page/Page column 19

3
[ 904326-88-1 ]
[ 1222105-32-9 ]
[ 1222105-72-7 ]

Yield	Reaction Conditions	Operation in experiment
61%	With sodium carbonate In 1,4-dioxane; water at 20℃; for 3.5h; Reflux; Inert atmosphere;	16.1 Sodium carbonate (2.40 g, 22.7 mmol) and tetrakis triphenylphosphine palladium (0.44 g, 0.38 mmol) were added to a 1,4-dioxane (44.0 ml)-water (22.0 ml) mixture solution of 2-chloro-9-(cyclopropylmethyl)-6-morpholin-4-yl-9H-purine (2.22 g, 7.56 mmol) and 2-methylaminopyrimidine-5-boronic acid pinacol ester (2.31 g, 9.82 mmol) at room temperature and the resulting mixture was heated to reflux for 3.5 hours in an argon atmosphere. The reaction mixture was left standing to cool and then poured into water and ethyl acetate was added to separate the layers. The solid precipitated in the aqueous layer was collected by filtration, washed with water, and then dried at 50° C. under reduced pressure. Meanwhile, the organic layer was dried over anhydrous sodium sulfate, the mixture was filtrated, then the filtrate was concentrated under reduced pressure, and the resulting solid was washed with dichloromethane and collected by filtration. These solids were combined to give the title compound (1.68 g, 61%) as a white solid.1H-NMR (CDCl3) δ: 0.47-0.52 (2H, m), 0.63-0.69 (2H, m), 1.28-1.37 (1H, m), 3.09 (3H, d, J=5.15 Hz), 3.84-3.88 (4H, m), 4.06 (2H, d, J=7.45 Hz), 4.27-4.45 (4H, brm), 5.24-5.34 (1H, m), 7.82 (1H, s), 9.29 (2H, s).

Reference： [1]Current Patent Assignee: DAIICHI SANKYO COMPANY, LIMITED - US2010/130492, 2010, A1 Location in patent: Page/Page column 90

4
[ 904326-88-1 ]
[ 1222105-38-5 ]
[ 1222105-82-9 ]

Yield	Reaction Conditions	Operation in experiment
41%	With sodium carbonate In 1,4-dioxane; water for 3h; Inert atmosphere; Reflux;	18.3 1,4-Dioxane (40 ml), water (20 ml), and sodium carbonate (2 g, 19 mmol) were added to N-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-amine (1.45 g, 6.18 mmol) and 2-chloro-6-morpholin-4-yl-9-(tetrahydrofuran-3-ylmethyl)-9H-purine (2.0 g, 6.18 mmol) and the atmosphere in the reaction vessel was substituted with nitrogen. Tetrakis triphenylphosphine palladium (0.36 g, 0.31 mmol) was added, then the atmosphere in the reaction vessel was substituted with nitrogen again, and the resulting mixture was heated to reflux for 3 hours. The reaction mixture was partitioned with ethyl acetate and water, the organic layer was dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. Methylene chloride-ether was added to the residue and the insoluble matter was collected by filtration and dried to give the title compound (1.0 g, 41%) as a white solid.1H-NMR (CDCl3) δ: 1.71-1.78 (1H, m), 2.02-2.08 (1H, m), 2.95-2.99 (1H, m), 3.09 (3H, d, J=5.15 Hz), 3.66 (1H, dd, J=8.88, 4.87 Hz), 3.76-3.81 (2H, m), 3.85-3.87 (4H, m), 3.94-3.99 (1H, m), 4.17 (1H, dd, J=13.75, 8.02 Hz), 4.23 (1H, dd, J=14.03, 7.73 Hz), 4.35 (4H, s), 5.29-5.32 (1H, m), 7.70 (1H, s), 9.28 (2H, s).

Reference： [1]Current Patent Assignee: DAIICHI SANKYO COMPANY, LIMITED - US2010/130492, 2010, A1 Location in patent: Page/Page column 93-94

5
[ 904326-88-1 ]
[ 944401-95-0 ]
[ 1254697-44-3 ]

Yield	Reaction Conditions	Operation in experiment
	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; sodium carbonate In 1,2-dimethoxyethane; water at 120℃; for 0.166667h; Microwave irradiation;

Reference： [1]Burger, Matthew T.; Knapp, Mark; Wagman, Allan; Ni, Zhi-Jie; Hendrickson, Thomas; Atallah, Gordana; Zhang, Yanchen; Frazier, Kelly; Verhagen, Joelle; Pfister, Keith; Ng, Simon; Smith, Aaron; Bartulis, Sarah; Merrit, Hanne; Weismann, Marion; Xin, Xiaohua; Haznedar, Joshua; Voliva, Charles F.; Iwanowicz, Ed; Pecchi, Sabina [ACS Medicinal Chemistry Letters, 2011, vol. 2, # 1, p. 34 - 38]

6
[ 904326-88-1 ]
[ 1369485-77-7 ]
[ 1369484-95-6 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate In tetrahydrofuran at 90℃; for 16h;	27 Method 27: Synthesis of {5-r5-((R)-l-Cvclopropyl-l-{5-ri-(tetrahvdro-pyran-4-yl)- lH-pyrazol^-yll^l^^loxadiazol-S-yll-ethv -pyridin^-yll-pyrimidin^-v -methyl- amine Example 169)1-36.5 R-30 Example 169To a pressure tube is added 1-36.5 (213 mg, 0.53 mmol), R-30 (150 mg, 0.64 mmol), Tetrakis(triphenylphosphine)palladium (0) (61 mg, 0.053 mmol) and 2M aq. Na2C03 (1 ml, 2 mmol) in THF (8 ml). The reaction mixture is stirred at 90 °C for 16 hours. The reaction mixture is conecntrated in vacuo. The residue is diluted with EtOAc, is washed with water, brine, is dried under anhy. Na2S04, and is filtered and concentrated. The residue is purified by flash chromatography (Si02, 0-5% MeOH/CH2Cl2) to afford the title compound (131 mg); m/z 473.4 [M+l]

Reference： [1]Current Patent Assignee: C.H. Boehringer Sohn AG & Co. KG - WO2012/40137, 2012, A1 Location in patent: Page/Page column 122

7
[ 904326-88-1 ]
[ 1339925-58-4 ]
[ 1339925-65-3 ]

Yield	Reaction Conditions	Operation in experiment
43%	With bis-triphenylphosphine-palladium(II) chloride In ethanol; water; toluene at 90℃; for 3h; Inert atmosphere;	100.100a Step 100a: Ethyl 5-(tert-butoxycarbonyl(2-(2-(methylamino)pyrimidin-5-yl)-4-morpholinothieno[3,2-d]pyrimidin-6-yl)amino)pentanoate (Compound 1103-227) Step 100a: Ethyl 5-(tert-butoxycarbonyl(2-(2-(methylamino)pyrimidin-5-yl)-4-morpholinothieno[3,2-d]pyrimidin-6-yl)amino)pentanoate (Compound 1103-227)[0651]A mixture of 1102-226 (300 mg, 0.6 mmol), N-methyl-5-(4,4,5,5-tetra methyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-amine (0602-227) (645 mg, 4.22 mmol) and Pd(PPh3)2Cl2 (12.7 mg) in a mixed solvents of toluene (6 mL), ethanol (4 mL) and water (1 mL) was stirred at 90° C. for 3 h under N2 atmosphere. After the completion of the reaction (monitored by TLC), the reaction mixture was concentrated and the residue was purified by column chromatography eluted with methanol in dichloromethane to afford title product as a colorless oil (150 mg, 43%). 1HNMR (400 MHz, DMSO-d6): δ 1.16 (t, J=7.2 Hz, 3H), 1.53 (s, 9H), 1.60-1.80 (m, 4H), 2.36 (t, J=6.4 Hz, 2H), 2.87 (d, J=4.8 Hz, 3H), 3.78 (t, J=4.4 Hz, 4H), 3.90-3.96 (m, 6H), 4.04 (q, J=7.2 Hz, 2H), 6.99 (s, 1H), 7.52 (d, J=4.8 Hz, 1H), 9.14 (br, 2H).

Reference： [1]Current Patent Assignee: CURIS INC - US2013/102595, 2013, A1 Location in patent: Paragraph 0650; 0651

8
[ 904326-88-1 ]
[ 1476076-22-8 ]
C₁₉H₂₁N₇O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium diacetate; sodium carbonate In water; isopropyl alcohol at 120℃; for 0.5h; Inert atmosphere; Microwave irradiation;	6.v Example 6 Preparation (S)-N-(2-(2,3-dihydrofuro[3,2-b]pyridin-7-yl)propyl)-6-(6-(methylamino)pyridin-3-yl)pyrimidin-4-amine (Compound 430) As shown in step 6-v of Scheme 6, (S)-6-chloro-N-(2-(2,3-dihydrofuro[3,2-b]pyridin-7-yl)propyl)pyrimidin-4-amine (29.2 mg, 0.1003 mmol), N-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine (30.7 mg, 0.2006 mmol), Na2CO3 (150.4 μL of 2 M aqueous solution, 0.3009 mmol), and i-PrOH (2.0 mL) were combined and flushed with nitrogen gas for 10 minutes. SPhos (water soluble, 10.28 mg, 0.0201 mmol) and Pd(OAc)2 (1.13 mg, 0.0050 mmol) were added and the reaction vessel sealed and heated to 120° C. in a microwave for 30 minutes. The reaction mixture was filtered over diatomaceous earth and the filtrate was concentrated under reduced pressure. The residue was purified by reversed-phase HPLC (0-30% CH3CN/H2O, 0.1% TFA). The TFA salt obtained was neutralized using a StratoShperes PL-HCO3 MP-Resin cartridge to provide (S)-N-(2-(2,3-dihydrofuro[3,2-b]pyridin-7-yl)propyl)-6-(6-(methylamino)pyridin-3-yl)pyrimidin-4-amine (Compound 430, 23.8 mg, 65% yield): LCMS=364.12 (M+H); 1H NMR (400 MHz, DMSO-d6) δ 8.83 (s, 2H), 8.41 (s, 1H), 7.90 (d, J=5.1 Hz, 1H), 7.55 (s, 1H), 7.39 (s, 1H), 7.01 (s, 1H), 6.77 (s, 1H), 4.61 (t, J=8.4 Hz, 2H), 3.66-3.40 (m, 2H), 3.26-3.12 (m, 3H), 2.86 (d, J=4.5 Hz, 3H), 1.21 (d, J=6.6 Hz, 3H).

Reference： [1]Current Patent Assignee: VERTEX PHARMACEUTICALS (OLD) - US2013/281431, 2013, A1 Location in patent: Paragraph 0251

9
[ 904326-88-1 ]
(S)-6-chloro-N-[2-(2,3-dihydro-[1,4]dioxino[2,3-b]pyridin-8-yl)propyl]pyrimidin-4-amine [ No CAS ]
(S)-N⁶-(2-(2,3-dihydro-[1,4]dioxino[2,3-b]pyridin-8-yl)propyl)-N²'-methyl-[4,5'-bipyrimidine]-2',6-diamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; sodium carbonate In isopropyl alcohol at 80℃;	7.vi Example 7 Preparation of (S)-N⁶-(2-(2,3-dihydro-[1,4]dioxino[2,3-b]pyridin-8-yl)propyl)-N²′-methyl-[4,5′-bipyrimidine]-2′,6-diamine (Compound 462) As shown in step 7-vi of Scheme 7,6-chloro-N-[2-(2,3-dihydro-[1,4]dioxino[2,3-b]pyridin-8-yl)propyl]pyrimidin-4-amine (410 mg) was dissolved in IPA (0.75 mL). N-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-amine (23 mg) was added, followed by the addition of 2M Na2CO3 (122 μL) and 1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II), dichloromethane complex (7 mg). The reaction vessel was sealed and heated at 80° C. overnight. The mixture was cooled, diluted with ethyl acetate, washed with water, dried over Na2SO4, filtered, concentrated under reduced pressure and purified by reversed-phase HPLC, 5-50% ACN/H2O/0.1% TFA. Fractions containing pure product were collected, dissolved in MeOH, passed through a carbonate cartridge, and concentrated under reduced pressure to provide (S)-N6-(2-(2,3-dihydro-[1,4]dioxino[2,3-b]pyridin-8-yl)propyl)-N2′-methyl-[4,5′-bipyrimidine]-2′,6-diamine (Compound 462): ESMS=380.39 (M+H); 1H NMR (300 MHz, methanol-d4) δ 8.75 (s, 2H), 8.47 (s, 1H), 7.65 (d, J=5.3 Hz, 1H), 6.94 (d, J=5.2 Hz, 1H), 6.76 (s, 1H), 4.46-4.34 (m, 2H), 4.32-4.19 (m, 2H), 3.59 (ddd, J=12.0, 11.5, 7.3 Hz, 3H), 2.99 (s, 3H), 1.32 (d, J=6.7 Hz, 3H).

Reference： [1]Current Patent Assignee: VERTEX PHARMACEUTICALS (OLD) - US2013/281431, 2013, A1 Location in patent: Paragraph 0259

10
[ 904326-88-1 ]
[ 1616290-27-7 ]
[ 1616290-50-6 ]

Yield	Reaction Conditions	Operation in experiment
74%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; sodium carbonate In 1,4-dioxane at 100℃; for 1h; Inert atmosphere;	128 A solution of 4-[2-(benzyloxy)-4,6-dimethylpyridin-3-yl]methyl}-9-bromo-6-methyl-7-(propan-2-yloxy)-3,4-dihydro-1,4-benzoxazepin-5(2H)-one (116 g, 121 mg, 0.224 mmol), N-m ethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-amine (52.7 mg, 0.224 mmol) and sodium carbonate (2.0 M, 71.2 mg, 0.672 mmol) in 1,4-dioxane (2.0 mL) was degassed (N2) for 5 min, then PdCl2(dppf)-DCM (50.0 mg, 0.0610 mmol) was added. The reaction was heated at 100° C. for 1 hour. The reaction was diluted with water (25 mL) and EtOAc (25 mL). The layers were separated and the organic phase was dried with magnesium sulfate and concentrated under vacuum. The residue was purified by column chromatography (silica gel, heptanes/EtOAc) to give 4-[2-(benzyloxy)-4,6-dimethylpyridin-3-yl]methyl}-6-methyl-9-[2-(methylamino)pyrimidin-5-yl]-7-(propan-2-yloxy)-3,4-dihydro-1,4-benzoxazepin-5(2H)-one (128a, 94 mg, 74% yield) as a white solid.

Reference： [1]Current Patent Assignee: PFIZER INC - US2014/179667, 2014, A1 Location in patent: Paragraph 0962; 0963

11
[ 904326-88-1 ]
N-(4-bromo-3-[(dimethylamino)methylidene]sulfamoyl}phenyl)-2-(2-chlorophenyl)acetamide [ No CAS ]
2-(2-chlorophenyl)-N-(3-[(dimethylamino)methylidene]sulfamoyl}-4-[2-(methylamino)pyrimidin-5-yl]phenyl)acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium fluoride; bis(triphenylphosphine)palladium(II) dichloride; triphenylphosphine In propan-1-ol; water at 100℃; for 1h; Inert atmosphere;	301 2-(2-Chlorophenyl)-N-{4-[2-(methylamino)pyrimidin-5-yl]-3- sulfamoylphenyl}acetamide N-(4-Bromo-3-[(dimethylamino)methylidene]sulfamoyl}phenyl)-2-(2-chlorophenyl)-acetamide (250 mg, 545 pmol) and N-methyl-5-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2- yl)pyrimidin-2-amine (256 mg, 1.1 mmol) were dissolved in n-propanol (8.1 ml) and bis(triphenylphosphine)palladium(l I) dichloride (CAS 13965-03-2) (19.2 mg, 27.2 pmol), triphenylphosphine (5.4 p1, 27 pmol), potassium fluoride (7.91 mg, 136 pmol) and aqueouspotassium phosphate (540 p1, 2.0 M, 1.1 mmol) were added. The solution was purged with argon for 5 minutes and the reaction was heated at 100°C for lh in the microwave. Afterwards the mixture was filtered over Celite, the solvent was removed under reduced pressure and the crude was used without further purification in the next step.

Reference： [1]Current Patent Assignee: BAYER AG - WO2017/191000, 2017, A1 Location in patent: Page/Page column 402

12
[ 904326-88-1 ]
(R)-3-bromo-5-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)pyridine [ No CAS ]
(R)-5-(5-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)pyridin-3-yl)-N-methylpyrimidin-2-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
28%	With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In 1,4-dioxane at 90℃; for 2h; Inert atmosphere;	45 4.1.15 3-((2,4-dichlorobenzyl)oxy)-5-(5-(piperidin-1-ylmethyl)thiophen-2-yl)pyridine (15) General procedure: A reaction solution of 3-bromo-5-((2,4-dichlorobenzyl)oxy)pyridine (12a) (150.00mg, 0.45mmol) and 1-((5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophen-2-yl)methyl)piperidine (13c) (138.27mg, 0.45mmol) in 1,4-dioxane (15.00mL) was purged with nitrogen. Then PdCl2(PPh3)2 (15.44mg, 0.022mmol) and 1.0M of Na2CO3 (143.08mg, 1.35mmol) aqueous solution were added. The resulting mixture was purged with nitrogen and stirred at 90°C for 2h. The reaction mixture was filtered through a Celite pad and washed well with MeOH. The residue was partitioned between DCM and saturated aqueous NaHCO3 solution and brine. The organic layer was dried over MgSO4 and concentrated in vacuo and the resulting crude mixture was purified by a silica gel column, eluting with EA:Hexane (1:1) to collect the title product (15) as a yellow solid (116.00mg, 59%)

Reference： [1]Lim, Ji Woong; Kim, Seok Kyu; Choi, Seo Yun; Kim, Dong Hoi; Gadhe, Changdev G.; Lee, Hae Nim; Kim, Hyo-Ji; Kim, Jina; Cho, Sung Jin; Hwang, Hayoung; Seong, Jihye; Jeong, Kyu-Sung; Lee, Jae Yeol; Lim, Sang Min; Lee, Jae Wook; Pae, Ae Nim [European Journal of Medicinal Chemistry, 2018, vol. 157, p. 405 - 422]

13
[ 904326-88-1 ]
(S)-3-bromo-5-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)pyridine [ No CAS ]
(S)-5-(5-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)pyridin-3-yl)-N-methylpyrimidin-2-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
6%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; caesium carbonate In 1,2-dimethoxyethane at 90℃; for 2h; Inert atmosphere;	49 4.1.14 3-((2,4-dichlorobenzyl)oxy)-5-(thiophen-2-yl)pyridine (14) General procedure: A reaction solution of 3-bromo-5-((2,4-dichlorobenzyl)oxy)pyridine (12a) (120.00mg, 0.36mmol) and 4,4,5,5-tetramethyl-2-(thiophen-2-yl)-1,3,2-dioxaborolane (13b) (75.64mg, 0.36mmol) in DME (15.00mL) was purged with nitrogen. Then Pd (dppf)Cl2CH2Cl2 (12.53mg, 0.015mmol) and 1.0M of Cs2CO3 (351.89mg, 1.08mmol) aqueous solution were added. The resulting mixture was purged with nitrogen and stirred at 90°C for 2h. The reaction mixture was filtered through a Celite pad and washed well with MeOH. The residue was partitioned between DCM and saturated aqueous NaHCO3 solution and brine. The organic layer was dried over MgSO4 and concentrated in vacuo and the resulting crude mixture was purified by a silica gel column, eluting with EA:Hexane (1:1) to collect the title product (14) as a white solid (72.00mg, 36%);

14
[ 904326-88-1 ]
tert-butyl N-[3-chloro-6-fluoro-4-[3-(trifluoromethyl)pyrazol-1-yl]-9H-pyrido[2,3-b]indol-8-yl]-N-ethylcarbamate [ No CAS ]
C₂₇H₂₆F₄N₈O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium phosphate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; XPhos In 1,4-dioxane; water at 100℃; for 12h; Inert atmosphere;

Reference： [1]Hu, Yimin; Shi, Houguang; Zhou, Mingwei; Ren, Qingcheng; Zhu, Wei; Zhang, Weixing; Zhang, Zhiwei; Zhou, Chengang; Liu, Yongqiang; Ding, Xiao; Shen, Hong C.; Yan, S. Frank; Dey, Fabian; Wu, Waikwong; Zhai, Guanglei; Zhou, Zheng; Xu, Zhiheng; Ji, Ying; Lv, Hua; Jiang, Tianyi; Wang, Wen; Xu, Yunhua; Vercruysse, Maarten; Yao, Xiangyu; Mao, Yi; Yu, Xiaomin; Bradley, Kenneth; Tan, Xuefei [Journal of Medicinal Chemistry, 2020, vol. 63, # 17, p. 9623 - 9649]

15
[ 904326-88-1 ]
3-(p-bromophenyl)-5-hydroxy-5-trifluoromethyl-Δ²-isoxazoline [ No CAS ]
3-{4-[2-(methylamino)pyrimidin-5-yl]phenyl}-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-5-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
39%	With dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II); caesium carbonate In 1,4-dioxane; water at 85℃; for 1h;	3-{4-[2-(Methylamino)pyrimidin-5-yl]phenyl)-5-(trifluoromethyl)-4,5-dihydro-1 ,2-oxazol-5-ol (compound I-001) To N-methyl-5-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)pyrimidin-2-amine (83 mg, 0.35 mmol) and [1 ,1 -Bis(di-tert-butylphosphino)ferrocene]dichloropalladium (II) (10 mg, 0.016 mmol) were added a solution of cesium carbonate (1 15 mg, 0.35 mmol) in water (0.8 ml) and a solution of 3-(4-bromophenyl)- 5-(trifluoromethyl)-4,5-dihydro-1 ,2-oxazol-5-ol (100 mg, 0.32 mmol) in dioxane (2.4 ml). The mixture was stirred at 85°C for 1 h and then cooled to rt. The reaction mixture was then concentrated and diluted with dichloromethane. The suspension was given onto a 2g silica cartridge, eluted with dichloromethane and evaporated. The residue was purified using preparative HPLC-MS (SunFire Waters, 30*150, 5 pm, eluent: acetonitrile/water (0.1 % formic acid)) to afford the title compound (43 mg, 39% yield). MS (ESI): 339 ([M+H]+)

Reference： [1]Current Patent Assignee: BAYER AG - WO2020/254486, 2020, A1 Location in patent: Page/Page column 57-58

16
[ 904326-88-1 ]
2-bromo-5-(2,6-dichloro-4-methoxyphenyl)thiophene [ No CAS ]
5-[5-(2,6-dichloro-4-methoxyphenyl)thiophen-2-yl]-N-methylpyrimidin-2-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
10%	With potassium phosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ In 1,4-dioxane; water at 80℃; for 3h;	3.5 Step 5. 5-[5-(2,6-Dichloro-4-methoxyphenyl)thiophen-2-yl]-N-methylpyrimidin-2-amine A solution of 2-bromo-5-(2,6-dichloro-4-methoxyphenyl)thiophene (45.0 mg, 0.133 mmol), N-methyl-5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)pyrimidin-2-amine (37.5 mg, 0.160 mmol), Pd(dppf)CI2CH2CI2(21.7 mg, 0.027 mmol) and K3PO4 (84.7 mg, 0.399 mmol) in 1,4-dioxane (1.00 mL) and H2O (0.50 mL) was stirred for 3 h at 80 °C under nitrogen atmosphere. The reaction mixture was cooled to 25 °C and concentrated under vacuum. The residue was purified by Pre-TLC (eluting with 1 :4 ethyl acetate/petroleum ether) to give a crude product. The crude product was purified via Prep-HPLC (Column, XBridge Shield RP18 OBD Column, 19 x 150 mm 5 um; Mobile phase, A: water (containing 0.05% TFA) and B: ACN (50% to 75% in 8 min); Detector, UV 220/254 nm). The collected fraction was lyophilized to afford 5-[5-(2,6-dichloro-4-methoxyphenyl)thiophen-2-yl]-N-methylpyrimidin-2-amine as an off-white solid (5.10 mg, 10%). 1H-NRR (DMSO-d6, 400 MHz) δ (ppm): 8.74 (s, 2H), 7.54- 7.39 (m, 2H), 7.23 (s, 2H), 7.09-6.98 (m, 1H), 3.86 (s, 3H), 2.85 (s, 3H). LCMS (ES, m/z): 366 [M+H]+
10%	With potassium phosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ In 1,4-dioxane; water at 80℃; for 3h;	3.5 Step 5. 5-[5-(2,6-Dichloro-4-methoxyphenyl)thiophen-2-yl]-N-methylpyrimidin-2-amine A solution of 2-bromo-5-(2,6-dichloro-4-methoxyphenyl)thiophene (45.0 mg, 0.133 mmol), N-methyl-5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)pyrimidin-2-amine (37.5 mg, 0.160 mmol), Pd(dppf)CI2CH2CI2(21.7 mg, 0.027 mmol) and K3PO4 (84.7 mg, 0.399 mmol) in 1,4-dioxane (1.00 mL) and H2O (0.50 mL) was stirred for 3 h at 80 °C under nitrogen atmosphere. The reaction mixture was cooled to 25 °C and concentrated under vacuum. The residue was purified by Pre-TLC (eluting with 1 :4 ethyl acetate/petroleum ether) to give a crude product. The crude product was purified via Prep-HPLC (Column, XBridge Shield RP18 OBD Column, 19 x 150 mm 5 um; Mobile phase, A: water (containing 0.05% TFA) and B: ACN (50% to 75% in 8 min); Detector, UV 220/254 nm). The collected fraction was lyophilized to afford 5-[5-(2,6-dichloro-4-methoxyphenyl)thiophen-2-yl]-N-methylpyrimidin-2-amine as an off-white solid (5.10 mg, 10%). 1H-NRR (DMSO-d6, 400 MHz) δ (ppm): 8.74 (s, 2H), 7.54- 7.39 (m, 2H), 7.23 (s, 2H), 7.09-6.98 (m, 1H), 3.86 (s, 3H), 2.85 (s, 3H). LCMS (ES, m/z): 366 [M+H]+

Reference： [1]Current Patent Assignee: PAKINAX - WO2022/31, 2022, A1 Location in patent: Page/Page column 67; 69
[2]Current Patent Assignee: PAKINAX - WO2022/31, 2022, A1 Location in patent: Page/Page column 67; 69

17
[ 32779-36-5 ]
[ 73183-34-3 ]
[ 904326-88-1 ]

Yield	Reaction Conditions	Operation in experiment
93%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate In 1,4-dioxane at 80℃; for 3h;	3.2 Step 2. N-methyl-5-(4,4,5,5-tetramethyl-l,3,2-dioxabon>lan-2-yl)pyrimidm-2-amine A mixture of 5-bromo-N-methylpyrimidin-2-amine (1.00 g, 5.31 mmol), 4,4,5,5-tetra- methyl-2-(tetramethyl-l,3,2-dioxaborolan-2-yl)-l,3,2-dioxaborolane (1.62 g, 6.38 mmol), Pd(dppf)CI2CH2CI2(0.430 g, 0.532 mmol) and KOAc (1.57 g, 15.9 mmol) in 1,4-dioxane (10.0 mL) was stirred for 3 h at 80 °C under nitrogen atmosphere. The mixture was allowed to cool down to 20 °C. The reaction was quenched by the addition of water (60 mL). The resulting mixture was extracted with ethyl acetate (3 x 50 mL). The organic layers were combined, washed with brine (50 mL), dried over anhydrous sodium sulfate, filtered and concentrated under vacuum. The residue was purified by silica gel column chromatography (eluting with 1:2 ethyl acetate/petroleum ether) to afford N-methyl-5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2- yl)pyrimidin-2-amine as a yellow oil (1.30 g, 93%). LCMS (ES, m/z): 236 [M+H]+.
93%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate In 1,4-dioxane at 80℃; for 3h;	3.2 Step 2. N-methyl-5-(4,4,5,5-tetramethyl-l,3,2-dioxabon>lan-2-yl)pyrimidm-2-amine A mixture of 5-bromo-N-methylpyrimidin-2-amine (1.00 g, 5.31 mmol), 4,4,5,5-tetra- methyl-2-(tetramethyl-l,3,2-dioxaborolan-2-yl)-l,3,2-dioxaborolane (1.62 g, 6.38 mmol), Pd(dppf)CI2CH2CI2(0.430 g, 0.532 mmol) and KOAc (1.57 g, 15.9 mmol) in 1,4-dioxane (10.0 mL) was stirred for 3 h at 80 °C under nitrogen atmosphere. The mixture was allowed to cool down to 20 °C. The reaction was quenched by the addition of water (60 mL). The resulting mixture was extracted with ethyl acetate (3 x 50 mL). The organic layers were combined, washed with brine (50 mL), dried over anhydrous sodium sulfate, filtered and concentrated under vacuum. The residue was purified by silica gel column chromatography (eluting with 1:2 ethyl acetate/petroleum ether) to afford N-methyl-5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2- yl)pyrimidin-2-amine as a yellow oil (1.30 g, 93%). LCMS (ES, m/z): 236 [M+H]+.

Reference： [1]Current Patent Assignee: PAKINAX - WO2022/31, 2022, A1 Location in patent: Page/Page column 67; 68
[2]Current Patent Assignee: PAKINAX - WO2022/31, 2022, A1 Location in patent: Page/Page column 67; 68

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Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
{[ item.p_purity ]}	{[ item.pr_size ]}	{[ getRatePrice(item.pr_usd, 1,1) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]}	{[ getRatePrice(item.pr_usd, 1,1) ]}	{[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate) ]}	{[ item.pr_usastock ]}	Inquiry -	{[ item.pr_chinastock ]}	Inquiry -

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 904326-88-1 ]

Quality Control of [ 904326-88-1 ]

Related Doc. of [ 904326-88-1 ]

Product Details of [ 904326-88-1 ]

Safety of [ 904326-88-1 ]

Application In Synthesis of [ 904326-88-1 ]

[ 904326-88-1 ] Synthesis Path-Downstream 1~17

Related Functional Groups of [ 904326-88-1 ]

Organoboron

Esters

Amines

Related Parent Nucleus of [ 904326-88-1 ]

Pyrimidines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 904326-88-1 ]

Related Parent Nucleus of
[ 904326-88-1 ]